A new synthetic method for the preparation of nucleoside phosphoramidate analogues with the nitrogen atom in bridging positions of the phosphoramidate linkage

Kers, Inger; Stawiński, Jacek; Kraszewski, Adam

doi:10.1016/s0040-4039(97)10734-1

Cited by 25 publications

(19 citation statements)

References 23 publications

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“…2 Nitrogenbridging phosphodiester mimics, where N-protonation becomes possible, have also been generated and studied. [3][4][5][6][7][8][9][10] A combination of N-and S-bridging systems have seen application in the form of phosphate triester mimics that show antiviral activity. These 30 uncharged, nucleoside-based thiophosphoramidates serve as prodrogs which traverse cell membranes, however, within the cell, programmed hydrolysis occurs to reveal nucleoside monophosphates that go on to interefere with viral replication.…”

Section: Introductionmentioning

confidence: 99%

Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing

Trmčić¹,

Chadbourne²,

Brear³

et al. 2013

Org. Biomol. Chem.

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(2013) 'Aqueous synthesis of N,S,-dialkylthiophosphoramidates : design, optimisation and application to library construction and antileishmanial testing. ', Organic and biomolecular chemistry., 11 (16). pp. 2660-2675. Further information on publisher's website:Publisher's copyright statement:Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. We recently reported the use of PSCl 3 for the thiophosphorylation of alkylamines where the resulting Nthiophosphoramidate ions could be readily S-alkylated (Chem. Commun., 2011, 47, 6156-6158.). Herein 10 we report the development of this methodology using amino acid, amino sugar, aminonucleoside and aniline substrates. The hydrolysis properties of N-thiophosphoramidate ions and their reactivities towards alkylating agents are also explored. In addition, we demonstrate the application of our approach to the preparation of a small library of compounds, including quinoline-based N,S-dialkylthiophosphoramidates which were tested for antileishmanial activity.15

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Section: Introductionmentioning

confidence: 99%

Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing

Trmčić¹,

Chadbourne²,

Brear³

et al. 2013

Org. Biomol. Chem.

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“…A plethora of effective chemical approaches have been devised for the preparation of phosphoramidates. [1,2,[15][16][17][18][19][20][21][22][23][24] Among these, two approaches are worthy of mention here. The first approach involves the condensation of dialkyl chlorophosphates with dialkylamines in the presence of a base.…”

Section: Introductionmentioning

confidence: 99%

N,N′-Dichlorobis(2,4,6-trichlorophenyl)urea (CC-2): an Efficient Reagent for the Synthesis of Chemical Weapons Convention-Related Dialkyl-N,N-dialkylphosphoramidates from Dialkylphosphites

et al. 2007

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The present paper describes the one-pot synthesis of dialkyl N,N-dialkylphosphoramidates (DADAP) from dialkylphosphites and dialkylamines using N,N -dichlorobis(2,4,6-trichlorophenyl)urea (CC-2) as chlorinating reagent. DADAP belong to the schedule 2.B.6 category of the Chemical Weapons Convention (CWC), as they are the important markers of the chemical warfare agent tabun and its analogues. The study was undertaken to develop the spectral database of DADAP for verification of CWC. The reported synthetic strategy can be adopted to rapidly synthesize several analogues of DADAP during official proficiency tests.

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“…Due to their higher stability, ease of handling, and efficiency in solid-phase synthesis, [6Ϫ8] H-phosphonothioate building blocks [1,9] seem to be superior to phosphorothioamidite derivatives [10] in the synthesis of nucleotide analogues with multiple modifications at the phosphorus centre that are difficult to prepare in other ways, for example from nucleoside phosphorodithioates, [6,7,11,12] nucleoside phosphoramidothioates, [13] nucleoside phosphorofluoridothioates, [14] etc. Despite their usefulness in the synthesis of various types of phosphorus compounds, there are only a handful of synthetic methods available for the preparation of nucleoside H-phosphonothioate monoesters.…”

Section: During the Last Decade We Have Introduced And Have Been Invementioning

confidence: 99%

Silylation‐Mediated Transesterification of O‐Phenyl H‐Phosphonothioates − A New Entry to Nucleoside H‐Phosphonothioate Monoesters

2004

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A new synthetic method for the preparation of nucleoside phosphoramidate analogues with the nitrogen atom in bridging positions of the phosphoramidate linkage

Cited by 25 publications

References 23 publications

Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing

Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing

N,N′-Dichlorobis(2,4,6-trichlorophenyl)urea (CC-2): an Efficient Reagent for the Synthesis of Chemical Weapons Convention-Related Dialkyl-N,N-dialkylphosphoramidates from Dialkylphosphites

Silylation‐Mediated Transesterification of O‐Phenyl H‐Phosphonothioates − A New Entry to Nucleoside H‐Phosphonothioate Monoesters

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